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Volumn , Issue 5, 2000, Pages 743-753

Enantio- and diastereoselective synthesis of (protected) 2-formyl- and 2-(hydroxymethyl)-1-phenylalkane-1,3-diols from chiral 2-methoxy-3-tosyl-1,3- oxazolidines by subsequent asymmetric formylation and aldolization

Author keywords

Asymmetric formylation; Chiral 3 arensulfonyl 1,3 oxazolidines; Chiral alkane 1,3 diols; Chiral auxiliaries; Diastereoselective aldolization; Ketones; Titanium enolates

Indexed keywords

ALKANE; ETHER DERIVATIVE; KETONE; OXAZOLIDINE DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

EID: 0034078486     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6393     Document Type: Article
Times cited : (9)

References (65)
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    • For a similiar result with appropriate lithium and cesium enolates, see Ref. 2f.
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    • See Refs 7,8 for example
    • See Refs 7,8 for example.
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    • Examples for Lewis acid-catalyzed epimerization, see Refs 7,8.
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    • note
    • -3, Flack parameter 0.00(2), hydrogens calculated and riding.
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    • Note, that - compared to "ordinary" silyl enol ethers - the CIP-assignment is inverted due to the high priority of the oxazolidine residue
    • Note, that - compared to "ordinary" silyl enol ethers - the CIP-assignment is inverted due to the high priority of the oxazolidine residue.
  • 53
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    • The appropriate unlike diastereoisomers (2R,1′S or 2S,1′R) exhibit J = 8.0-9.0 Hz
    • The appropriate unlike diastereoisomers (2R,1′S or 2S,1′R) exhibit J = 8.0-9.0 Hz.
  • 60
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    • note
    • -3, Flack parameter 0.04(2), hydrogens calculated and riding. Data sets were collected with an Enraf Nonius CAD4 diffractometer. Programs used: data reduction MoIEN, structure solution SHELXS-97, structure refinement SHELXL-97, graphics SCHAKAL-92. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CSD-138306 (anti-8d) and CSD-138307 (anti-11b). Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: int. Code +44(1223)336033, e-mail: deposit@ccdc.cam.ac.uk].
  • 65
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    • The enantiomeric series is formed from (S)-N-tosylamino alkanols, derived from naturally occuring amino acids; see Refs 7,8
    • The enantiomeric series is formed from (S)-N-tosylamino alkanols, derived from naturally occuring amino acids; see Refs 7,8.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.